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Synfacts 2018; 14(12): 1297
DOI: 10.1055/s-0037-1611332
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Phosphoric Acid Catalyzed Four-Component Ugi Reaction

Contributor(s):
Benjamin List
,
Oleg Grossmann
Zhang J, Yu P, Li S.-Y, Sun H, Xiang S.-H, Wang J, Houk KN. * Tan B. * Southern University of Science and Technology, Shenzhen, P. R. of China and University of California, Los Angeles, USA
Asymmetric Phosphoric Acid-Catalyzed Four-Component Ugi Reaction.

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Publication History

Publication Date:
19 November 2018 (online)

 
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Key words

Ugi reaction - acylamino amides - chiral phosphoric acids

Significance

The Houk and Tan groups report an asymmetric phosphoric acid catalyzed Ugi reaction furnishing α-aminoacylaminoamides from four achiral building blocks in excellent yields and high enantioselectivities. DFT calculations support imine activation accomplished by phosphoric acid carboxylic acid heterodimer catalysis through a bifunctional activation mode.


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Comment

Asymmetric Ugi reactions, which are highly atom- and step-economical transformations, remain challenging partially due to the requirement of suppressing the Passerini reaction. The authors have developed two chiral phos­phoric acids, based on STRIP (I. Čorić, S. Müller, B. List J. Am. Chem. Soc. 2010, 132, 17370) that fully suppress the Passerini reaction while providing a broad substrate scope.


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